Basic information
- Standard SMILES
CC(C)OC(=O)/N=N/C(=O)OC(C)C- InChIKey
VVWRJUBEIPHGQF-MDZDMXLPSA-N- Molecular formula
- C8H14N2O4
- Average molar mass
- 202.21 g/mol
- Monoisotopic mass
- 202.09535693
Names & identifiers
- Preferred name
- Diisopropyl azodicarboxylate
- IUPAC
- propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate
- English name
- Diisopropyl azodicarboxylate
- Molecular formula
- C8H14N2O4
- Molecular weight
- 202.21
Names & synonyms
Diisopropyl azodicarboxylate2446-83-5Diisopropyl azodiformate939987-56-1Diisopropyl azodicarboxylate [MI]Formic acid, azodi-, diisopropyl ester7W701BXX4KEINECS 219-502-81,2-Diazenedicarboxylic acid 1,2-bis(1-methylethyl) esterDTXSID50894754Diazenedicarboxylic acid, bis(1-methylethyl) esterRefChem:587897
Show more names
diisopropyl (E)-diazene-1,2-dicarboxylateDisopropyl AzodicarboxylateAZODICARBONIC ACID DIISOPROPYL ESTER(E)-diisopropyl diazene-1,2-dicarboxylateDiisopropyl azodicarboxylate [DIAD]Propan-2-yl N-propan-2-yloxycarbonyliminocarbamateDIAD(Diisopropylazodicarboxylate)
DTXCID4013243121,2Diazenedicarboxylic acid 1,2bis(1methylethyl) ester219-502-8DiisopropylazodicarboxylateDIADDiisopropyl diazene-1,2-dicarboxylateMFCD00008875propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate
Database identifiers
- CAS
2446-83-5、939987-56-1- PubChem CID
- 5363146
- DTXSID
DTXSID50894754- UNII
- 7W701BXX4K
- EC Number
- 219-502-8
- Nikkaji
- J3.771.302C、J56.134G
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 77.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 211
Experimental & physicochemical properties
Physical DescriptionOrange liquid; [Merck Index] Pungent odor; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 3 · 3-5 °C
- Boiling point
- 75 °C/0.25 · 75 °C/0.25 mmHg (lit.)
- Density
- 1.027 g/mL · 1.027 g/mL at 25 °C (lit.)
- vapor pressure
- 1.04 hPa · 1.04 hPa (20 °C)
- refractive index
- 20 · n20/D 1.420(lit.)
- Flash point
- 223 °F · 223 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Liquid
- color
- Clear to slightly turbid yellow-orange to red
- Water Solubility
- insoluble
- Sensitive
- Light Sensitive
- BRN
- 1912326 · 1912326
- InChI
- InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3
- InChIKey
- VVWRJUBEIPHGQF-UHFFFAOYSA-N
- SMILES
- N(C(OC(C)C)=O)=NC(OC(C)C)=O
- CAS DataBase Reference
- 2446 · 2446-83-5(CAS DataBase Reference)
- FDA UNII
- 7 W701BXX4K · 7W701BXX4K
- UNSPSC Code
- 12352302 · 12352302
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS08,GHS09
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335-H351-H411
- Precautionary statements
- 202 · P202-P261-P273-P302+P352-P305+P351+P338-P308+P313
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,Xi,N,F
- Risk Statements
- 36 · 36/38-51/53-5-43-36/37/38-11-48/20/22-40
- Safety Statements
- 36 · 36-61-47A-36/37/39-29-26-16-60-36/37
- RIDADR
- 3082 · UN 3082 9/PG 3
- WGK Germany
- 1 · 1
- F
- 4.1 · 4.10-8
- Hazard Note
- Harmful/Irritant
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 29270000 · 29270000
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Carc · Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2STOT RE 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 35.9% (52 of 145) of reports.
Warning
H315 (62.8%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (62.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (61.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H373 (54.5%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H411 (61.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P260, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 145 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 52 of 145 reports by companies.；There are 20 notifications provided by 93 of 145 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
Regulatory Information
Status: Active Update: 02-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23916
Diisopropylazodicarboxylate: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin, respiratory tract, and strong eye irritant; [Alfa Aesar MSDS] See Diethyl azodicarboxylate.
Hazard Classes and CategoriesSkin Irrit. 2 (62.8%)；Eye Irrit. 2 (62.8%)；STOT SE 3 (61.4%)；STOT RE 2 (54.5%)；Aquatic Chronic 2 (61.4%)
Regulatory information
Regulatory Information
Status: Active Update: 02-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23916
Diisopropylazodicarboxylate: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 4.10-8
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- ridadr
- UN 3082 9/PG 3
- hs_code
- 29270000
- risk_code
- 36/38-51/53-5-43-36/37/38-11-48/20/22-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- Xn,Xi,N,F
- hazard_note
- Harmful/Irritant
- safety_code
- 36-61-47A-36/37/39-29-26-16-60-36/37
- hazard_class
- 9
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H351-H411
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2STOT RE 2STOT SE 3
- Precautionary statements
- P202-P261-P273-P302+P352-P305+P351+P338-P308+P313
Chemistry & industry
Uses & manufacturing
UsesUsed as a reagent; [Merck Index]
Applications
UsesIt can be used as dye intermediates, pharmaceutical intermediates, organic synthesis reagents, and the foaming agent of the rubber plastics liquid. Isopropyl azodicarboxylate can be used for the liquid foaming agent of vinyl resin. It can be used to make light-colored vinyl foam. It has a uniform pore structure with different formulations and processing conditions giving foam of either closed pore or open pore. It can also be used as pharmaceutical intermediates, and organic synthesis reagents.
UsesDiisopropyl Azodicarboxylate is an azodicarboxylic acid derivative used as a reagent in the production of many organic compounds. Diisopropyl Azodicarboxylate is commonly used as an oxidizer in Mitsun obu reactions and can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.
UsesDiisopropyl azodicarboxylate is used as an important reagent in the production of many organic compounds. It is used in association with triphenyl phosphine in Mitsunobu reaction of alcohols, acids and amides. It acts as reactant in the preparation of chromenes resembling classical cannabinoids, norbornene-based guanidine-rich polymers and acceptor-donor-acceptor organic dyes.
General DescriptionReacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.
Upstream & downstream products
Upstream raw materials
Downstream products
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