3-({[bis(propan-2-yl)amino](chloro)phosphanyl}oxy)propanenitrile

• ChemBase ID: 92949
• Molecular Formular: C9H18ClN2OP
• Molecular Mass: 236.678781
• Monoisotopic Mass: 236.08452752
• SMILES: N(P(OCCC#N)Cl)(C(C)C)C(C)C
• Canonical SMILES: CC(N(P(OCCC#N)Cl)C(C)C)C
• InChI: InChI=1S/C9H18ClN2OP/c1-8(2)12(9(3)4)14(10)13-7-5-6-11/h8-9H,5,7H2,1-4H3
• InChIKey: QWTBDIBOOIAZEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({[bis(propan-2-yl)amino](chloro)phosphanyl}oxy)propanenitrile
• IUPAC Traditional name: 3-{[chloro(diisopropylamino)phosphanyl]oxy}propanenitrile
• Synonyms: Chloro(diisopropylamino)-β-cyanoethoxyphosphine; 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite; 2-Cyanoethyl diisopropylchlorophosphoramidite; Cyanoethyl N,N-Diisopropyl Phosphoamidochloridite; 2-Cyanoethyl n,n-Diisopropylchlorophosphoramidite; 2-Cyanoethyl bis(prop-2-yl)phosphoramidochloridoite; 2-Cyanoethyl N,N-bis(isopropyl)chlorophosphoramidite; 氯代(二异丙基氨基)-β-氰基乙氧基膦; 2-氰乙基N,N-二异丙基氯亚磷酰胺; 2-氰基乙基 二异丙基氯代亚磷酰胺

Database IDs

• CAS Number: 89992-70-1
• MDL Number: MFCD00011544
• Beilstein Number: 3588525
• PubChem SID: 24882318; 24858245; 162079647
• PubChem CID: 2734844

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8914871
• LogD (pH = 7.4): 2.0151713
• Log P: 2.017
• Molar Refractivity: 62.0107 cm^3
• Polarizability: 23.965153 Å^3
• Polar Surface Area: 36.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Benzene; Dichloromethane
• Apperance: Slightly Hazy Yellow Liquid
• Boiling Point: 103-104°C/0.08 mm; 103-105°C/0.08mm; 103-105°C/0.08mm
• Flash Point: >110°C; >110°C(230°F); 110 °C; 230 °F
• Density: 1.061; 1.061 g/mL at 25 °C(lit.)
• Refractive Index: 1.478; 1.4780; n20/D 1.479

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere Refrigerator
• Storage Warning: Corrosive/Harmful/Moisture Sensitive/Store under Argon/Store at -20°C; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2845; UN3265
• German water hazard class: 3
• Hazard Class: 4.2; 8
• Packing Group: 1; II
• Risk Statements: 5-22-34; 5-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H250-H314; H314-H318-H302
• GHS Precautionary statements: P222-P231-P280-P305 + P351 + P338-P310-P422; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2845 4.2/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.5% (T); 95%
• Grade: purum
• Compostion: Cl, 13.5-15.5%
• Shipped in: wet ice
• Linear Formula: [(CH3)2CH]2NP(Cl)OCH2CH2CN

DETAILS

Apollo Scientific Ltd - OR9800T

A protecting reagent in DNA synthesis. Also a phosphorylating agent.

Sigma Aldrich - 302309

Application
Phosphitylating reagent for 3′-hydroxyl groups for use in the synthesis of oligodeoxyribonucleotides.1,2,3,4
Used in a scalable, solution-phase oligonucleotide synthesis employing phosphoramidite chemistry and DMT-, iBu- and Bz-protected monomers. Intermediates were isolated by extraction without further purification.
Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 63229

Caution
may become turbid on storage
Other Notes
Phosphorylating agent used in the phosphoramidite method1,2,3,4,5

Toronto Research Chemicals - C980000

A protecting reagent in DNA synthesis. Also a phosphorylating agent.

REFERENCES

• Tetrahedron Lett., 24, 5843 (1983)
• Tetrahedron Lett., 27, 1211 (1986)
• Phosphitylating agent for use in oligonucleotide synthesis by the phosphite triester method: Tetrahedron Lett., 24, 5843 (1983); 27, 1211 (1986).