(E)-1-[(dimethylcarbamoyl)imino]-3,3-dimethylurea

• ChemBase ID: 102403
• Molecular Formular: C6H12N4O2
• Molecular Mass: 172.18508
• Monoisotopic Mass: 172.09602564
• SMILES: CN(C)C(=O)/N=N/C(=O)N(C)C
• Canonical SMILES: CN(C(=O)/N=N/C(=O)N(C)C)C
• InChI: InChI=1S/C6H12N4O2/c1-9(2)5(11)7-8-6(12)10(3)4/h1-4H3
• InChIKey: VLSDXINSOMDCBK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (E)-1-[(dimethylcarbamoyl)imino]-3,3-dimethylurea; 1-[(dimethylcarbamoyl)imino]-3,3-dimethylurea
• IUPAC Traditional name: (E)-1-[(dimethylcarbamoyl)imino]-3,3-dimethylurea; tetramethylazoformamide; tetramethylazodicarboxamide
• Synonyms: 1,1′-Azobis(N,N-dimethylformamide); N,N,N′,N′-Tetramethylazodicarboxamide; Diazenedicarboxylic acid bis(N,N-dimethylamide); Diamide; Azodicarboxylic acid bis(dimethylamide); Diazine dicarboxylic acid bis-(N,N-dimethylamide)]; 1,1'-Azobis(N,N-dimethylformamide);N,N,N',N'-Tetramethylazodicarboxamide; TMAD; DIAMIDE; 1,1'-Azobis(N,N-dimethylformamide); Tetramethylazodicarboxamide; Diamide; Tetramethyldiazenedicarboxamide; N,N,N′,N′-Tetramethylazoformamide 1,1'-Azobis(N,N-dimethylformamide); N,N,N′,N′-Tetramethylazobisformamide

Database IDs

• CAS Number: 10465-78-8
• EC Number: 233-951-7
• MDL Number: MFCD00008318
• Beilstein Number: 1910409
• PubChem SID: 24888957; 162088104; 24278365
• PubChem CID: 5353800; 4278
• Wikipedia Title: Tetramethylazodicarboxamide

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.95128554
• LogD (pH = 7.4): -0.95128554
• Log P: -0.95128554
• Molar Refractivity: 42.672 cm^3
• Polarizability: 16.021149 Å^3
• Polar Surface Area: 65.34 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow crystalline; Yellow crystalline solid
• Melting Point: 113–115 °C; 113-115°C

Safety Information

• Storage Condition: -20°C
• RTECS: LQ1041000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (CHN)
• Linear Formula: (CH3)2NCON=NCON(CH3)2

DETAILS

MP Biomedicals - 02101527

Used as a thiol oxidizing agent.

Sigma Aldrich - D3648

Application
Reported to be of use as a thiol oxidizing agent. Diamide has been used to titrate protein glutathiolation to discriminate from other oxidative protein modifications. Treatment increased protein glutathiolation in a concentration-dependent manner and had comparably little effect on protein-protein disulfide formation.1

Sigma Aldrich - 87751

Other Notes
Reagent for Mitsunobu reactions of acids with high pK′s 1; synthesis of cyclic ethers from diols2

REFERENCES

• Kosower, N.S., et al., Biochem. Biophy. Res. Commun., 37: 593 (1969).