N,N,N',N'-Tetramethylazodicarboxamide

HCID 4278
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Substructure searchFind similar structures

Basic information

CAS
10465-78-8
Standard SMILES
CN(C)C(=O)N=NC(=O)N(C)C
InChIKey
VLSDXINSOMDCBK-UHFFFAOYSA-N
Molecular formula
C6H12N4O2
Average molar mass
172.19 g/mol
Monoisotopic mass
172.09602562

Names & identifiers

Preferred name
N,N,N',N'-Tetramethylazodicarboxamide
IUPAC
3-(dimethylcarbamoylimino)-1,1-dimethylurea
English name
N,N,N',N'-Tetramethylazodicarboxamide
Molecular formula
C6H12N4O2
Molecular weight
172.19

Names & synonyms

10465-78-8N,N,N',N'-TetramethylazodicarboxamideDTXSID6040456CHEBI:48958RefChem:1090319DTXCID40204561,1'-azobis(N,N-dimethylformamide)N1,N1,N2,N2-Tetramethyldiazene-1,2-dicarboxamideMFCD000083181,1'-azobis(N,N'-dimethylformamide)(3E)-3-(dimethylcarbamoylimino)-1,1-dimethyl-ureaN,N,N',N'-Tetramethylazodicarboxamide(TMAD)
Show more names
TMADDIAMIDE(E)-1-[(dimethylcarbamoyl)imino]-3,3-dimethylurea(E)-N1,N1,N2,N2-tetramethyldiazene-1,2-dicarboxamide3-(Dimethylcarbamoylimino)-1,1-dimethylureaNsc143013
C6H12N4O2TetramethylazodicarboxamideN,N',N'-TetramethylazodicarboxamideLopac0_000397SCHEMBL39340MLS002153343SCHEMBL103289orb1219154

Database identifiers

CAS
10465-78-8
PubChem CID
4278
DTXSID
DTXSID6040456
ChEMBL
CHEMBL1338900
EC Number
233-951-7

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
65.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biochemical Research
Physical DescriptionYellow crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
112 °C · 112 °C
Boiling point
220.4 · 220.4±23.0 °C(Predicted)
Density
1.13 · 1.13±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
soluble in Methanol
form
crystalline

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 29-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/29433
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (50%)

Safety data

F
4.10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
LQ1041000
hs_code
29270000
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesA sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells. [ChemIDplus]
Applications · 2 items

DescriptionN,N,N’,N’-Tetramethylazodicarboxamide (also named as Diamide, TMAD) is a reagent used for the oxidization of thiols in proteins. It is used as a reagent in the Mitsunobu reaction in place of diethyl azodicarboxylate. It can be used to titrate protein gluotathiolation to discriminate from other protein modifications.

UsesReported 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.

Upstream & downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
Changzhou Carman Chemical Co., Ltd.15061933924

Additional notes

DefinitionChEBI: 1,1'-azobis(N,N-dimethylformamide) is a monoazo compound.

Related reactions

176 records
New reaction record

Compound notes

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