Product Name

  • Name

    BIS(2-ETHYLHEXYL) PHOSPHITE

  • EINECS 222-904-6
  • CAS No. 3658-48-8
  • Article Data18
  • CAS DataBase
  • Density g/cm3
  • Solubility
  • Melting Point
  • Formula C16H35 O3 P
  • Boiling Point 395.2°Cat760mmHg
  • Molecular Weight 306.426
  • Flash Point 192.8°C
  • Transport Information
  • Appearance
  • Safety Poison by intravenous route. Moderately toxic by intraperitoneal route. An eye irritant. When heated to decomposition it emits toxic fumes of POx. See also ESTERS.
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3658-48-8 (BIS(2-ETHYLHEXYL) PHOSPHITE)
  • Hazard Symbols
  • Synonyms Bis(2-ethylhexyl)hydrogen phosphite;Bis(2-ethylhexyl) phosphite;Bis(2-ethylhexyl) phosphonate;Bis(2-ethylhexyl) phosphonic acid;Chelex H 8;Di-2-Ethylhexyl phosphite;Di-2-ethylhexyl hydrogen phosphite;Diisooctyl phosphite;NSC 2664;Phosphonicacid di(2-ethylhexyl) ester;
  • PSA 59.00000
  • LogP 5.84210

Synthetic route

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

Conditions
ConditionsYield
With phosphorus trichloride In benzene at 20℃; for 2h; Condensation;96%
With phosphorus trichloride at 20℃; for 2h;85.8%
With phosphonic acid; toluene
methyl phosphite
96-36-6, 868-85-9

methyl phosphite

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

Conditions
ConditionsYield
With sodium at 160℃;
2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

Conditions
ConditionsYield
With sodium at 160℃;
With sodium hydride In mineral oil at 160℃;
2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

diphenylphosphonate

diphenylphosphonate

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

Conditions
ConditionsYield
2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

mono-2-ethyl-1-hexyl phosphite

mono-2-ethyl-1-hexyl phosphite

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

Conditions
ConditionsYield
Stage #1: mono-2-ethyl-1-hexyl phosphite With phosphorus pentoxide at 54℃; for 3h; Inert atmosphere;
Stage #2: 2-Ethylhexyl alcohol at 56℃; for 0.5h; Inert atmosphere;
46.2 %Spectr.
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

bis(2-ethylhexyl) phosphorochloridate
63449-80-9

bis(2-ethylhexyl) phosphorochloridate

Conditions
ConditionsYield
With N-chloro-succinimide at -78 - 20℃; Inert atmosphere; neat (no solvent);97%
With chlorine
With sulfuryl dichloride
benzophenone
119-61-9

benzophenone

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

C29H45O4P

C29H45O4P

Conditions
ConditionsYield
Stage #1: benzophenone; bis(2-ethylhexyl)phosphite With calcium fluoride for 0.0833333h;
Stage #2: With potassium hydroxide at 40 - 50℃; for 2.16667h;
97%
formaldehyd
50-00-0

formaldehyd

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

benzylamine
100-46-9

benzylamine

O,O-di(2-ethylhexyl) 1-(benzylamino)methylphosphonate

O,O-di(2-ethylhexyl) 1-(benzylamino)methylphosphonate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 12h; Heating;95%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

butanone
78-93-3

butanone

C20H43O4P

C20H43O4P

Conditions
ConditionsYield
Stage #1: bis(2-ethylhexyl)phosphite; butanone With calcium fluoride for 0.0833333h;
Stage #2: With potassium hydroxide at 40 - 50℃; for 2.16667h;
92.5%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

dibutylamine
111-92-2

dibutylamine

bis(2-ethylhexyl) dibutylphosphoramidate

bis(2-ethylhexyl) dibutylphosphoramidate

Conditions
ConditionsYield
With tetrachloromethane In hexane Todd-Atherton reaction;88%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

acetone
67-64-1

acetone

benzylamine
100-46-9

benzylamine

O,O-di(2-ethylhexyl) 1-(benzylamino)-1-methylethylphosphonate

O,O-di(2-ethylhexyl) 1-(benzylamino)-1-methylethylphosphonate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 80℃; for 12h;87%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

diethylamine
109-89-7

diethylamine

bis(2-ethylhexyl) diethylphosphoramidate

bis(2-ethylhexyl) diethylphosphoramidate

Conditions
ConditionsYield
With tetrachloromethane at 0 - 20℃; for 1.5h; Todd-Atherton reaction;87%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

N-butylamine
109-73-9

N-butylamine

bis(2-ethylhexyl) butylphosphoramidate
53796-11-5

bis(2-ethylhexyl) butylphosphoramidate

Conditions
ConditionsYield
With tetrachloromethane In hexane Todd-Atherton reaction;86%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

phenylpropynoic acid ethyl ester
2216-94-6

phenylpropynoic acid ethyl ester

(E)-ethyl 2-(bis(2-ethylhexyloxy)phosphoryl)-3-phenylacrylate

(E)-ethyl 2-(bis(2-ethylhexyloxy)phosphoryl)-3-phenylacrylate

Conditions
ConditionsYield
With tributylphosphine In acetonitrile at 20℃; for 1.16667h; stereoselective reaction;84%
cobaltocene
1277-43-6

cobaltocene

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

bis[cyclopentadienyltris(bis(2-ethylhexyl) phosphito-P)cobalt-O,O',O'']cobalt(II)

bis[cyclopentadienyltris(bis(2-ethylhexyl) phosphito-P)cobalt-O,O',O'']cobalt(II)

Conditions
ConditionsYield
In neat (no solvent) byproducts: cyclopentadiene; (N2); 140°C, 40 h; removal of cyclopentadiene by distn., stirring with MeOH, filtration, drying (reduced pressure), chromy. (SiO2; hexane, then MeOH), evapn., dissoln. (hexane), membrane filtration, evapn.;83%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

1-hexyl-3-methylimidazol-1-ium chloride
171058-17-6

1-hexyl-3-methylimidazol-1-ium chloride

1-hexyl-3-methylimidazolium bis(2-ethylhexyl)phosphate

1-hexyl-3-methylimidazolium bis(2-ethylhexyl)phosphate

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In dichloromethane for 24h;82%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

2-Chloro-N,N-diethylacetamide
2315-36-8

2-Chloro-N,N-diethylacetamide

bis(2-ethyl-1-hexyl) (N,N-diethylcarbamoylmethyl)phosphonate
66258-31-9

bis(2-ethyl-1-hexyl) (N,N-diethylcarbamoylmethyl)phosphonate

Conditions
ConditionsYield
With potassium hydroxide; potassium carbonate In benzene for 6h; Product distribution; Ambient temperature; other diarylphosphine oxides and dialkyl hydrogen phosphites, var. alkylating agents, var. reaction times, also in the presence 18-crown-6, and phase transfer catalysis;80%
With potassium hydroxide; potassium carbonate In benzene for 6h; Ambient temperature;80%
With sodium hydroxide; Aliquat 336 In dichloromethane at 20 - 25℃; for 5.5h; Yield given;
(E)-2-decenol
18409-18-2

(E)-2-decenol

bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

(2E)-dec-2-en-1-yl bis(2-ethylhexyl) phosphate
1542073-82-4

(2E)-dec-2-en-1-yl bis(2-ethylhexyl) phosphate

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In tetrachloromethane; dichloromethane; water at 0℃; for 35h; Inert atmosphere;80%
bis(2-ethylhexyl)phosphite
3658-48-8

bis(2-ethylhexyl)phosphite

tert-Butyl chloroacetate
107-59-5

tert-Butyl chloroacetate

[Bis-(2-ethyl-hexyloxy)-phosphoryl]-acetic acid tert-butyl ester
103717-36-8

[Bis-(2-ethyl-hexyloxy)-phosphoryl]-acetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0 - 5℃; for 5h;79%

Bis(2-ethylhexyl) phosphite Consensus Reports

Reported in EPA TSCA Inventory.

Bis(2-ethylhexyl) phosphite Specification

Bis(2-ethylhexyl) phosphite, its CAS register number is 3658-48-8. And it is also named as Diisooctyl phosphite; Bis(2-ethylhexyl) phosphite; Di-2-ethylhexyl phosphite; Bis(2-ethyl-1-hexyl) phosphite; Bis(2-ethylhexyl) phosphonate; CID6327514; Phosphonic acid, bis(2-ethylhexyl) ester; Dioctyl (2-ethylhexyl) phosphite; Di-2-ethylhexylhydrogenphosphite and so on. Bis(2-ethylhexyl) hydrogen phosphite is colorless oily liquid and commonly used as fine chemical and pharmaceutical intermediate.

Physical properties about Bis(2-ethylhexyl) phosphite are: (1)ACD/LogP: 7.1; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.10; (4)ACD/LogD (pH 7.4): 7.09; (5)ACD/BCF (pH 5.5): 146371.10; (6)ACD/BCF (pH 7.4): 142135.90; (7)ACD/KOC (pH 5.5): 173365.70; (8)ACD/KOC (pH 7.4): 168349.40; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 15; (12)Flash Point: 192.825 °C; (13)Enthalpy of Vaporization: 70.832 kJ/mol; (14)Boiling Point: 395.225 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C16H35O3P.C2H6/c1-5-9-11-15(7-3)13-18-20(17)19-14-16(8-4)12-10-6-2;1-2/h15-16,20H,5-14H2,1-4H3;1-2H3;
(2)InChIKey=RIUIJOAYLGPGSH-UHFFFAOYSA-N;
(3)SmilesC([C@@H](CCCC)CC)OP(OC[C@@H](CCCC)CC)=O.CC;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 700mg/kg (700mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
AMA Archives of Industrial Health. Vol. 18, Pg. 464, 1958.
mouse LD50 intraperitoneal 620mg/kg (620mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
AMA Archives of Industrial Health. Vol. 18, Pg. 464, 1958.
rabbit LD50 intravenous 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
AMA Archives of Industrial Health. Vol. 18, Pg. 464, 1958.
rabbit LD50 skin 4500mg/kg (4500mg/kg)   Albright & Wilson Inc. Vol. #OPB-3, Pg. 1984,
rat LC50 inhalation > 20gm/m3 (20000mg/m3)   Albright & Wilson Inc. Vol. #OPB-3, Pg. 1984,
rat LD50 intraperitoneal 1500mg/kg (1500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
AMA Archives of Industrial Health. Vol. 18, Pg. 464, 1958.
rat LD50 oral 11900mg/kg (11900mg/kg)   Albright & Wilson Inc. Vol. #OPB-3, Pg. 1984,

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