Di-tert-butyl azodicarboxylate (HCID 97268)

Names & identifiers

Preferred name: Di-tert-butyl azodicarboxylate
IUPAC: tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate
English name: Di-tert-Butyl azodicarboxylate
Molecular formula: C10H18N2O4
Molecular weight: 230.26

Names & synonyms

Di-tert-butyl azodicarboxylate870-50-8DTXSID201306310RefChem:586103DTXCID201736276212-796-9Di-tert-butyl diazene-1,2-dicarboxylateAzodicarboxylic Acid Di-tert-butyl EsterDi-tert-butylazodicarboxylateMFCD00015001di-t-butyl azodicarboxylate(E)-di-tert-butyl diazene-1,2-dicarboxylate

Show more names

di-tert-butyl (E)-diazene-1,2-dicarboxylateDi-tert-Butyl azodicDi-tert-butyl azodiformateSKL270NSC 109889DI-TERT-BUTYL AZODICARBOXYALTEBis(tert-butoxycarbonyl)diazene

Di-(tert-butyl) diazene-1,2-dicarboxylate1,2-Diazenedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) esterDTADdi-tert-butylazocarboxylatetert-butyl {[(tert-butyl)oxycarbonyl]diazenyl}formatetert-butyl N-tert-butoxycarbonyliminocarbamatedi t-butyl azodicarboxylateDitertbutyl azodicarboxylate

Database identifiers

CAS: 870-50-8
PubChem CID: 97268
DTXSID: DTXSID201306310
EC Number: 212-796-9

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 77.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 16
Formal charge: 0
Complexity: 267

Physicochemical properties

Melting point: 89 · 89-92 °C(lit.)
Boiling point: 287.1 · 287.1±9.0 °C(Predicted)
Density: 1.06 · 1.06±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Crystals or Crystalline Powder
color: Yellow
Water Solubility: Insoluble
Sensitive: Light Sensitive
BRN: 1911434 · 1911434
InChI: InChI=1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3
InChIKey: QKSQWQOAUQFORH-VAWYXSNFSA-N
SMILES: N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O
CAS DataBase Reference: 870 · 870-50-8(CAS DataBase Reference)
UNSPSC Code: 12352108 · 12352108
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07,GHS08
Signal word: Danger
Hazard statements: 225 · H225-H304-H315-H320-H332-H335-H336-H360-H370-H372-H401-H319
Precautionary statements: 201 · P201-P202-P210-P233-P240-P241+P242+P243-P260-P264-P270-P271-P273-P280-P301+P310+P331-P302+P352+P332+P313+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P307+P311-P403+P233-P405-P261-P280a-P304+P340-P305+P351+P338-P501a
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi,F
Risk Statements: 36 · 36/37/38-11
Safety Statements: 26 · 26-36-37/39-16
RIDADR: 1325 · 1325
WGK Germany: 3 · 3
Hazard Note: Irritant
HazardClass: 3 · 3
PackingGroup: II
HS Code: 29270000 · 29270000
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 10.7% (6 of 56) of reports.

Warning

H315 (89.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (89.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (87.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 56 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 6 of 56 reports by companies.；There are 7 notifications provided by 50 of 56 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (89.3%)；Eye Irrit. 2 (89.3%)；STOT SE 3 (87.5%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
ridadr: 1325
hs_code: 29270000
risk_code: 36/37/38-11
Signal word: Danger
Symbol(GHS): GHS02,GHS07,GHS08
hazard_code: Xi,F
hazard_note: Irritant
safety_code: 26-36-37/39-16
hazard_class: 3
Storage Class: 11 - Combustible Solids
packing_group: II
Hazard statements: H225-H304-H315-H320-H332-H335-H336-H360-H370-H372-H401-H319
Precautionary statements: P201-P202-P210-P233-P240-P241+P242+P243-P260-P264-P270-P271-P273-P280-P301+P310+P331-P302+P352+P332+P313+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P307+P311-P403+P233-P405-P261-P280a-P304+P340-P305+P351+P338-P501a

Chemistry & industry

Applications · 4 items

UsesDi-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates via photoorganocatalytic hydroacylation of dialkyl azodicarboxylates with aldehydes in presence of phenylglyoxylic acid as photocatalyst.

UsesDi-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.

UsesUtilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.

General DescriptionDi-tert-butyl azodicarboxylate is a an acid labile reagent for Mitsunobu reactions allowing facile isolation of products and for the electrophilic amination and hydrazination of enolates and lithium alkyls.