Basic information
- CAS
102691-36-1- Standard SMILES
CC(C)N(C(C)C)P(OCCC#N)N(C(C)C)C(C)C- InChIKey
RKVHNYJPIXOHRW-UHFFFAOYSA-N- Molecular formula
- C15H32N3OP
- Average molar mass
- 301.41 g/mol
- Monoisotopic mass
- 301.22829927
Names & identifiers
- Preferred name
- 2-Cyanoethyl tetraisopropylphosphorodiamidite
- IUPAC
- 3-bis[di(propan-2-yl)amino]phosphanyloxypropanenitrile
- English name
- 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
- Molecular formula
- C15H32N3OP
- Molecular weight
- 301.41
Names & synonyms
Show more names
Database identifiers
- CAS
102691-36-1- PubChem CID
- 128153
- DTXSID
DTXSID8075176- UNII
- 8P2H5F3TEA
- EC Number
- 600-337-9
- Nikkaji
- J738.473D
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 39.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 273
Physicochemical properties
- Boiling point
- 100 °C0.5 · 100 °C0.5 mm Hg(lit.)
- Density
- 0.949 g/mL · 0.949 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.470(lit.)
- Flash point
- 141 °F · 141 °F
- storage temp.
- -20 °C · -20°C
- solubility
- Acetonitrile (Slightly), Benzene, Chloroform (Sparingly), Methanol (Slightly)
- form
- liquid
- pka
- 6.78 · 6.78±0.70(Predicted)
- color
- colorless
- Sensitive
- moisture sensitive, store cold
- BRN
- 3590103 · 3590103
- Stability
- Explodes When Heated
- InChI
- 1S/C15H32N3OP/c1-12(2)17(13(3)4)20(19-11-9-10-16)18(14(5)6)15(7)8/h12-15H,9,11H2,1-8H3
- InChIKey
- RKVHNYJPIXOHRW-UHFFFAOYSA-N
- SMILES
- CC(C)N(C(C)C)P(OCCC#N)N(C(C)C)C(C)C
- LogP
- 4.04 at · 4.04 at 20℃
- CAS DataBase Reference
- 102691 · 102691-36-1(CAS DataBase Reference)
- EPA Substance Registry System
- Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester (102691-36-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 226 · H226-H302-H317-H412
- Precautionary statements
- 210 · P210-P233-P273-P280-P301+P312-P303+P361+P353
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 5 · 5-36/37/38-42/43-36/38
- Safety Statements
- 3 · 3-26-36-24/25-23-45-36/37
- RIDADR
- 1993 · UN 1993 3/PG 3
- WGK Germany
- 3 · 3
- F
- 10 · 10-21-34
- Hazard Note
- Irritant/May Explode on Heating
- HazardClass
- 8 · 8
- PackingGroup
- I
- HS Code
- 29299000 · 29299000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3Flam. Liq. 3Skin Sens. 1B
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (97.2%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P370+P378, P403, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 179 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 01-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25176
Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 10-21-34
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- UN 1993 3/PG 3
- hs_code
- 29299000
- risk_code
- 5-36/37/38-42/43-36/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant/May Explode on Heating
- safety_code
- 3-26-36-24/25-23-45-36/37
- hazard_class
- 8
- Storage Class
- 3 - Flammable liquids
- packing_group
- I
- Hazard statements
- H226-H302-H317-H412
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 3Flam. Liq. 3Skin Sens. 1B
- Precautionary statements
- P210-P233-P273-P280-P301+P312-P303+P361+P353
Chemistry & industry
Applications
Description2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is a colorless viscous liquid, which is soluble in most organic solvents. It is a widely used phosphitylating reagent for the preparation of various phosphorylated biomolecules, such as nucleoside carbohydrate conjugates, phospholipids and glycopeptides. In particular, this reagent is highly effective for automated solid-phase DNA/RNA oligonucleotide synthesis. It has shown great utility in the coupling of nucleobases or carbohydrates via their phosphotriesters in the presence of activators such as 1H-tetrazole, in moderate yields under mild conditions.This compound is cheaper and more stable than 2-cyanoethyl N,N-diisopropylchlorophosphorodiamidite (the other commonly used phosphinylating reagent)[1].
UsesReagent for synthesizing phosphitylated nucleotides.1
Uses2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotideas phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserinein situ preparation of deoxyribonucleoside phosphoramiditesin preparation of 2′-deoxy-2′-fluoro-3′-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-5′-O-(4-methoxytrityl)-4′-thio-β-D-arabinouridine and 1-(3-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-2-deoxy-2-fluoro-5-O-(4,4′-dimethoxytrityl)-4-thio-β-D-arabinofuranosyl)-thymineas reagent for synthesizing phosphitylated nucleotides
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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