N,N-dimethylformamide

• ChemBase ID: 1614
• Molecular Formular: C3H7NO
• Molecular Mass: 73.09378
• Monoisotopic Mass: 73.05276385
• SMILES: CN(C)C=O
• Canonical SMILES: O=CN(C)C
• InChI: InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
• InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethylformamide
• IUPAC Traditional name: dimethylformamide
• Synonyms: N,N-Dimethylformamide, anhydrous; N,N-Dimethylformamide, anhydrous, amine free; N,N-Dimethylformamide, ACS; N,N-Dimethylformamide, Spectrophotometric Grade; N,N-Dimethylformamide, HPLC Grade; N,N-Dimethylmethanamide; Dimethylformamide; DMF; N-Formyldimethylamine; N,N-Dimethylformamide 99.8%; N,N-Dimethylformamide; N,N-DIMETHYLFORMAMIDE, HPLC/SPECTRO GRADE; N,N-DIMETHYLFORMAMIDE, ANHYDROSOLV GRADE; N,N-DIMETHYLFORMAMIDE, BIO GRADE; N,N-DIMETHYLFORMAMIDE; NCI-c60913; N,N-DIMETHYLFORMAMIDE ACS REAGENT GRADE; N,N-DIMETHYL FORMAMIDE; N,N-二甲基甲酰胺, 无水; N,N-二甲基甲酰胺, 无水, 无氨; N,N-二甲基甲酰胺, ACS; N,N-二甲基甲酰胺, 光谱级; N,N-二甲基甲酰胺, HPLC级; N,N-二甲基甲酰胺; N,N-二甲基甲酰胺, HPLC 级

Database IDs

• CAS Number: 68-12-2
• EC Number: 200-679-5
• MDL Number: MFCD00003284
• Beilstein Number: 605365
• Merck Index: 143243
• PubChem SID: 24872907; 160965071; 24853607; 24849479; 24867912; 24893883; 24865086; 24886401; 46506036; 24849438; 24878402; 24865091; 24859200; 24867382; 24883591; 24856379; 24859940
• PubChem CID: 6228
• CHEBI ID: 17741
• CHEMBL: 268291
• Chemspider ID: 5993
• DrugBank ID: DB01844
• KEGG ID: C03134
• MeSH Name: Dimethylformamide
• Unique Ingredient Identifier: 8696NH0Y2X
• Wikipedia Title: Dimethylformamide

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.63163495
• LogD (pH = 7.4): -0.6316349
• Log P: -0.6316349
• Molar Refractivity: 19.7688 cm^3
• Polarizability: 7.48225 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.77
• LOG S: 1.0
• Solubility (Water): 7.25e+02 g/l

PROPERTIES

Physical Property

• Solubility: 1000 mg/mL at 25 oC [ISHOW (NA--) @2ND]; Miscible in water
• Apperance: APHA: ≤15; clear; Colourless liquid; Liquid
• Melting Point: -60.45°C (212.7K); -60.5 °C; -61 °C(lit.); -61°C; -61°C
• Boiling Point: 151.85 - 153.85°C (425 - 427 K); 152 - 153 °C; 152-154 °C; 153 °C(lit.); 153°C; 153°C
• Flash Point: 136.4 °F; 57°C(135°F); 58 °C (closed cup and DIN 51755); 58 °C; 58°C
• Auto Ignition Point: 410 °C (DIN 51794); 445 °C; 833 °F
• Density: .94 g/cm^3 at 20 °C; 0.944; 0.944 g/mL(lit.); 0.948 g mL^-1; 0.948 g/mL at 20 °C; 0.948-0.950 g/mL at 20 °C
• Refractive Index: 1.4305 (at 20 °C); 1.431; 1.4310; n20/D 1.4290-1.4310; n20/D 1.430; n20/D 1.430(lit.); n20/D 1.431
• Vapor Pressure: .035 hPa at 20 °C; 2.7 mmHg ( 20 °C); 516 Pa
• Vapor Density: 2.5 (vs air); 2.51 (air = 1)
• Partition Coefficient: -0.829
• Absorption Wavelength: 270 nm; λ: 270 nm Amax: 1.00; λ: 275 nm Amax: 0.30; λ: 280 nm Amax: 0.25; λ: 290 nm Amax: 0.14; λ: 295 nm Amax: 0.10; λ: 300 nm Amax: 0.1; λ: 310 nm Amax: 0.05; λ: 320 nm Amax: 0.03; λ: 340 nm Amax: 0.005; λ: 340-400 nm Amax: 0.01
• Hydrophobicity(logP): -1.01 [HANSCH,C ET AL. (1995)]
• Viscosity: 0.92 mPa s (at 20 °C)
• Odor: fishy, ammoniacal
• Heat Capacity: 146.05 J K^-1 mol^-1
• Std enthalpy of combustion: -1.9428–-1.9404 MJ mol^-1
• Std enthalpy of formation: -240.6–-238.2 kJ mol^-1
• Absorbance: 1.00
• Transmittance: 270 nm, ≥20%; 280 nm, ≥70%; 300 nm, ≥90%; 310 nm, ≥89.2%; 330 nm, ≥98%

Safety Information

• Storage Condition: Room Temperature (15-30°C); Room Temperature (15-30°C), Avoid excess heat
• Storage Warning: Flammable/Harmful/Irritant/Teratogenic/Store under Argon; Hygroscopic
• RTECS: LQ2100000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 2265; UN2265
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Australian Hazchem: 2W
• Risk Statements: 61-20/21-36; R:10-20/21-36-61; r61, r20/21, r36
• Safety Statements: 53-45; S:16-45-53; s45
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 129
• TSCA Listed: 是
• EU Index: 616-001-00-X
• GHS Pictograms: GHS exclamation mark; GHS flame; GHS health hazard; GHS02; GHS07; GHS08
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  2

  2

  0
• LD50: 1.5 g kg^-1 (dermal, rabbit); 2.8 g kg^-1 (oral, rat)
• Explode Limits: 15.2 %; 2.2–15.2%
• GHS Hazard statements: 226, 312, 319, 332, 360; H226-H312 + H332-H319-H360D; H226-H312-H319-H332-H360D; H360-H226-H312-H332-H319
• GHS Precautionary statements: 280, 305+351+338, 308+313; P201-P280-P305 + P351 + P338-P308 + P313; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2265 3/PG 3

Product Information

• Purity: ≥99%; ~99%; ≥98.0% (GC); ≥99%; ≥99% (GC); ≥99.0%; ≥99.5%; ≥99.5% (GC); ≥99.8%; ≥99.8% (GC); ≥99.9%; ≥99.9% (GC); 99%; 99.7+%; 99.8%; 99.8+%; 99.9%
• Grade: absolute; ACS; ACS reagent; ACS spectrophotometric grade; analytical standard; anhydrous; B&J Brand (product of Burdick & Jackson); biotech. grade; CHROMASOLV® Plus; for HPLC; for molecular biology; for peptide synthesis; for residue analysis; for UV-spectroscopy; HPLC; JIS special grade; puriss.; puriss. p.a.; purum; REAGENT; ReagentPlus®; SAJ first grade; SPECTRANAL™
• Packaging: ampule of 1000 mg; packaged under Argon in resealable ChemSeal? bottles
• Suitability: GC-Headspace tested; passes test for IR spectroscopy; passes test for suitability for UV spectroscopy; suitable for neutral marker for measuring electroosmotic flow (EOF); suitable for solvent for chromogenic substrates (X-Gal, etc.) used in molecular biology applications.
• Evaporation Residue: <0.0005%; ≤0.0005%; ≤0.005%
• Impurities: <0.005% water; <8 ppm Free amines as dimethylamine; ≤0.0005 meq/g Titr. acid; ≤0.001% non-volatile matter; ≤0.003 meq/g Titr. base; ≤0.003% free acid (as CH3COOH); ≤0.003% Free acid (as CH3COOH); ≤0.005% free alkali (as NH3); ≤0.005% Free alkali (as NH3); ≤0.030% water; ≤0.05% water; ≤0.05% water (Karl Fischer); ≤0.08% water (Karl Fischer); ≤0.1% Water (Karl Fischer); ≤0.1% water (Karl Fischer); ≤0.15% water; ≤1 ppb fluorescence (quinine) at 254 nm; ≤1 ppb fluorescence (quinine) at 365 nm; ≤5 ng/L suitability for residue analysis
• Cation Traces: Al: ≤0.5 mg/kg; B: ≤0.02 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Li: ≥0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sn: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg; Zn: ≤0.2 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• Purified By: glass distillation
• Quality: for pesticide residue analysis; over molecular sieve (H2O ≤0.005%); over molecular sieve (H2O ≤0.01%)
• λ: 1 cm path, H2O reference; H2O reference
• abs.: /270 nm 1.00; /275 nm 0.30; /295 nm 0.10; /310 nm 0.05; /340 nm 0.010; /400 nm 0.010
• Appearance: APHA: ≤15
• Linear Formula: HCON(CH3)2

DETAILS

MP Biomedicals - 02195147

1 ml = ~0.94 g

MP Biomedicals - 02191417

ACS Reagent Grade
Specific Gravity: 0.944 g/ml
b.p. 152-154°C
Clear, liquid

MP Biomedicals - 02194818

Molecular Biology Reagent
Purity: 99+%
A solvent for chromogenic substrates in molecular biology experiments.

Sigma Aldrich - D8300

Application
多种疏水性有机化合物的溶剂。

Sigma Aldrich - 539465

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Solvent for many hydrophobic organic compounds.
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Sigma Aldrich - 34489

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Sigma Aldrich - 40245

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Solvent for many hydrophobic organic compounds.
General description
Special brochure (85475) available at cost price.
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Sigma Aldrich - 40249

Application
Solvent for many hydrophobic organic compounds.
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Packaging
tri Q-Multi-way barrel (further details see appendix)

Sigma Aldrich - 30576

Application
Solvent for many hydrophobic organic compounds.

Sigma Aldrich - D4551

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多种疏水性有机化合物的溶剂。
包装
250, 500 mL in glass bottle

Sigma Aldrich - 40240

Application
Solvent for many hydrophobic organic compounds.

Sigma Aldrich - 51781

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Solvent for many hydrophobic organic compounds.
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Watch a 6-minute presentation that demonstrates the effective use of our High Purity Solvents for GC Headspace Analysis
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tested for GC-HS
Protocols & Applications
The Utility of Headspace Grade Solvents for the Analysis of Organic Volatile Impurities

Sigma Aldrich - 40243

Application
Solvent for many hydrophobic organic compounds.
General description
no impurities present which would show greater signals than 5 ng/l lindane, in the GC/ECD retention time range of lindane to DDT

Sigma Aldrich - 227056

Application
Solvent for many hydrophobic organic compounds.
Packaging
1, 6×1, 2, 4×2 L in Sure/Seal™
View returnable container options.
100, 12×100 mL in Sure/Seal™
18, 200 L in Pure-Pac™ 1

Sigma Aldrich - 33120

Application
Solvent for many hydrophobic organic compounds.

Sigma Aldrich - 07-4430

Application
Solvent for many hydrophobic organic compounds.

Sigma Aldrich - D158550

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Solvent for many hydrophobic organic compounds.
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Sigma Aldrich - 72438

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Solvent for many hydrophobic organic compounds.

Sigma Aldrich - 40248

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Sigma Aldrich - 648531

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Solvent for many hydrophobic organic compounds.
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4×4 L in PVC coated
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Sigma Aldrich - 494488

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1, 6×1, 2 L in Sure/Seal™
10 L in ss drum
10 L packaged in closed-head stainless steel drums; 18 L, 56 L, 200 L packaged in Pure-Pac® stainless steel containers; 1 L, 2 L packaged in Sure/Seal™
18 L in Pure-Pac™ 1
20 L in Nowpak™ II
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56, 200, 400 L in Pure-Pac™ 1
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Sigma Aldrich - 270547

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Solvent for many hydrophobic organic compounds.
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1, 6×1, 2, 4×2, 4×4 L in glass bottle
10 L in ss drum
10 L packaged in closed-head stainless steel drums; 100 mL, 1 L, 2 L, 6×1 L, 4×2 L, 4×4 L packaged in glass bottles
100 mL in glass bottle
200 L in Pure-Pac™ 1
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CHROMASOLV is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 40246

Application
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General description
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Sigma Aldrich - 34903

Application
Solvent for many hydrophobic organic compounds.
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Sigma Aldrich - 442568

Application
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Sigma Aldrich - 437573

Application
Solvent for many hydrophobic organic compounds.
Packaging
18 L in VerSA-Flow™
4×4 L in PVC coated

Sigma Aldrich - 319937

Application
Solvent for many hydrophobic organic compounds.
Packaging
1, 6×1, 2, 2.5, 4, 4×4 L in glass bottle
20 L in steel drum
200 L in poly drum
500, 6×500 mL in glass bottle

Sigma Aldrich - 15440

Application
Solvent for many hydrophobic organic compounds.

Sigma Aldrich - 154814

Application
Solvent for many hydrophobic organic compounds.
Packaging
1, 6×1, 4×4 L in glass bottle

Sigma Aldrich - 40255

Application
Solvent for many hydrophobic organic compounds.

Sigma Aldrich - 40228

Application
Solvent for many hydrophobic organic compounds.

DrugBank - DB01844

• Drug Groups: experimental
• References: Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. [Pubmed]
• External Links: Wikipedia

Apollo Scientific Ltd - OR16840

For Peptide Synthesis

REFERENCES

• Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. Pubmed
• Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.
• In combination with POCl₃, (COCl)₂, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:
  
• Compare also N-Methylformanilide, A11829, and preformed Vilsmeier reagent (Chloromethylene)dimethylammonium chloride, B24172. Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994). Formylation can be extended to less active substrates, e.g. acenaphthene or mesitylene, with the DMF-triflic anhydride reagent: J. Chem. Soc., Chem. Commun., 1571 (1990). Under Vilsmeier conditions, electron-rich alkenes can be converted to ɑ?-unsaturated aldehydes; see, e.g.: Synthesis, 752 (1976); and ketones to ?-chloroenals: Synthesis, 496 (1985); Org. Synth. Coll., 5, 215 (1973).
• Vilsmeier conditions also promote dehydrations, e.g. in cyclodehydration of hydroxyphenols to give cyclic ethers, as an efficient alternative to the Mitsunobu reaction: J. Chem. Soc., Perkin 1, 2249 (1996); J. Org. Chem., 59, 4346 (1994):
  
• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.
• DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).
• In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).
• For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.